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Acetic Acid → Methyl 3-[1-(4-chlorobenzyl)-3-(1,1-dimethylethylthio)-5-(pyrid-2-ylmethoxy)indol-2-yl]-2,2-dimethylpropionate

HRID 1975740
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HRID 1975740 반응식
[C:1]([S:5][CH2:6][C:7](=O)[CH2:8][C:9]([CH3:15])([CH3:14])[C:10]([O:12][CH3:13])=[O:11])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.C([O-])(=O)C.[Na+].[Cl:26][C:27]1[CH:49]=[CH:48][C:30]([CH2:31][N:32]([C:34]2[CH:39]=[CH:38][C:37]([O:40][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=3)=[CH:36][CH:35]=2)N)=[CH:29][CH:28]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.CCCCCC.O>[Cl:26][C:27]1[CH:49]=[CH:48][C:30]([CH2:31][N:32]2[C:34]3[C:39](=[CH:38][C:37]([O:40][CH2:41][C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=4)=[CH:36][CH:35]=3)[C:6]([S:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[C:7]2[CH2:8][C:9]([CH3:15])([CH3:14])[C:10]([O:12][CH3:13])=[O:11])=[CH:29][CH:28]=1
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참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 14980531Methyl 5-t-butylthio-2,2-dimethyl-4-oxopentanoateHCID 190983301-(4-Chlorobenzyl)-1-[4-(pyrid-2-ylmethoxy)phenyl] hydrazine

생성물 1

HCID 19098332Methyl 3-[1-(4-chlorobenzyl)-3-(1,1-dimethylethylthio)-5-(pyrid-2-ylmethoxy)indol-2-yl]-2,2-dimethylpropionate

시약·촉매·용매 3

HCID 962Water용매
HCID 1140Toluene용매
HCID 21226206Ethyl acetate hexane용매

실험 절차

To a solution of methyl 5-t-butylthio-2,2-dimethyl-4-oxopentanoate (33.2 g; 135 mmol), prepared as in Example 1, step 4, in 300 mL toluene and 150 mL acetic acid was added sodium acetate (12.7 g; 155 mmol) followed by 1-(4-chlorobenzyl)-1-[4-(pyrid-2-ylmethoxy)phenyl] hydrazine (48.4 g; 143 mmol), prepared as in step 4. The reaction mixture was stirred in the dark for 5 days, then was poured into water and extracted with ethyl acetate. Solid sodium bicarbonate was added to the extracts and then filtered. The filtrate was washed with water, dried over magnesium sulfate, and the solvent was evaporated. The product was isolated by flash chromatography (40% diethyl ether in hexane) and then recystallized from ethyl acetate/hexane to yield methyl 3-[1-(4-chlorobenzyl)-3-(1,1-dimethylethylthio)-5-(pyrid-2-ylmethoxy)indol-2-yl]-2,2-dimethylpropionate.

후처리

  1. extractionextracted with ethyl acetate
  2. additionSolid sodium bicarbonate was added to the extracts
  3. filtrationfiltered
  4. washThe filtrate was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe product was isolated by flash chromatography (40% diethyl ether in hexane)

출처 및 근거

ORD 기록
ord-a48a416db2384b2880eeafea8ce50e51
출처 데이터셋
uspto-grants-1994_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05288743

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